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Palladium-Catalyzed Stereospecific Oxidative Cascade Reaction of Allenes for the Construction of Pyrrole Rings: Control of Reactivity and Selectivity
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Stockholm University, Faculty of Science, Department of Materials and Environmental Chemistry (MMK).
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-8462-4176
Number of Authors: 32019 (English)In: ACS Catalysis, ISSN 2155-5435, E-ISSN 2155-5435, Vol. 9, no 6, p. 5184-5190Article in journal (Refereed) Published
Abstract [en]

A palladium-catalyzed oxidative cascade reaction of alpha-tosylamide allenes has been developed. The reactivity of the allenes is controlled by the tosylamide group. In the presence of terminal alkynes the reaction proceeds via a pathway leading to a one-pot construction of pyrrole rings. Moreover, a solvent-controlled chemoselectivity of the cascade reaction was realized, leading to a stereospecific and divergent synthesis of (Z)-tetrasubstituted olefins, 2,5-dihydropyrroles, and pyrroles. Enantioenriched (Z)-tetrasubstituted olefins and 2,5-dihydropyrroles are readily synthesized by chirality transfer using this approach.

Place, publisher, year, edition, pages
2019. Vol. 9, no 6, p. 5184-5190
Keywords [en]
stereospecific, cascade reaction, nitrogen heterocycles, solvent-controlled selectivity, allenic amide
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:su:diva-171143DOI: 10.1021/acscatal.9b01041ISI: 000471212600046OAI: oai:DiVA.org:su-171143DiVA, id: diva2:1342469
Available from: 2019-08-13 Created: 2019-08-13 Last updated: 2019-08-13Bibliographically approved

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Li, Man-BoSvensson Grape, ErikBäckvall, Jan-E.
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